Right now my fiction-reading* is Among Thieves by Douglas Hulick, which I had heard from several sources as being the best fantasy book from a debut author in 2011. So far, I'm enjoying it, but it is definitely a cozy walk down some familiar road. The worldbuilding aspects are a bit more info-dumpish than I care for, but certainly workable-- especially given a first-person narrator that has an interest in history. But on the whole, it's an underworld romp with a thief-hero that does what it says on the tin.
I have to admit, I'm kind of fascinated by how common the thief-hero is in the fantasy genre. We have tons of them. Gray Mouser in Leiber. Prince Kheldar in Eddings. Vlad Taltos in Brust. Locke Lamora in Lynch. You could even make the argument for Bilbo Baggins as a thief-hero.
I'm not immune to it myself. Veranix in Thorn of Dentonhill certainly has thief-hero qualities, and Asti and Verci Rynax, as well as the rest of the Holver Alley Crew, are thief-heroes as well. In both cases, I at least try and subvert the trope a bit. Neither Veranix or the Rynax brothers are just work-a-day thieves in the guild. (It's always a guild, isn't it?) Not to say that's all other writers are doing, but that is the common trope, to the point that Pratchett specifically mocks it in Discworld.
But what is it about the charming scofflaw that appeals to us, as readers? Do we just love the bad boy? I don't think it is quite that simple. We (by which I mean audiences in general) do love to see an underdog win, especially if he does it in a fun way. Heist movies, of course, have the same appeal. We love to see someone beat the system by being clever.
But it's always a tricky balance to walk-- you want your thief-hero to do bad things, but never so far that you can't call him a hero. That's my hiccup with Hulick's book so far-- his main character starts out torturing someone for information. It's a bit hard to get on someone's side when that's how you first see him.
Any favorite thief-heroes that I didn't mention?
*- At any given time, I'm probably reading three different things: one fiction (Among Thieves), one non-fiction (The Edible History of Humanity) and one for-critique for a fellow writer (Elle Ven Hensbergen's latest, for which writing up my comments is on this week's to-do list).
Not a thief-hero favorite, but rather I have a comment on your theory. I think it is spot on (the underdog thing), particularly because many of us who enjoy the thief-hero are geeks. We know that the beautiful people, the people who understand how the systems of power work, can use their powers directly. But we have to be sneaky.
On top of that, the thief-hero hits our brains on a Jungian, archetypal level. He is like many Greek heroes, he is a trickster figure.
I think in part it's that of all the illegal things a character could do, thievery is perhaps the least reprehensible. Plus, it's easy to give a character a sympathetic reason to be a thief. So... if we're looking around for a character flaw that won't alienate the reader, willingness to commit thievery is an appealing option.
And yes, I'm guilty too. My next main character starts off as a con man.
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